When Is It The Right Time To Ask To Bring *That* Into The Boudoir?


Relationships are filled with benchmarks and goalposts. There’s the meeting which leads to the first date. Which if it goes well may lead to the first kiss or maybe just to a second date which will then presumably lead to the first kiss (depending on how conservative the individuals are).

There’s the first time you see the other person’s place. And the big marker, the first time you have sex. For many people that’s the first major landmark as you can go around kissing on anybody but you can’t just let anybody jiggle your jollies.

Of course you go from there to exclusivity then actual “official” relationships, possibly marriage, babies, student loans and then death. You know the usual.

But along the way there are various other landmarks, specifically depending on the individual. For instance, there’s the first time you ask somebody to…

…do anal. Or introduce sex toys. Or slap you on the hiney. Or heiny. Or hiny. I’ve never been sure how to spell that. Maybe it’s one of those words that doesn’t actually have a spelling since you’re just supposed to say it and not write it down.

How exactly does one even bring any of those things up. Anal, for example. It has to be one of those things that one party wants but fears bringing up for sounding sexually aggressive and nasty. You never know how folks feel about anal til you know, ya know? I imagine that convo goes like this:

Him: *thinking* Finally my chance. *outloud* They so crazy. Talking about anal! That’s crazy.
Her: You think that’s crazy? I’ve never tried that before. It creeps me out.
Him: Me too girl!!!! I’ve never done that either. How does one even do that?!?
Her: I mean it seems simple enough it just seems like it might hurt.
Him: You’re right. But they make all these different types of cream and jelly for it. You know, from what I hear. The things people do are crazy nowadays. Cuh-ray-zy.
Her: You sound like you’ve thought about this. Is that something you want to try?
Him: Absolutely not! I’m just saying. Sheesh…I mean…not unless…you want to, ya know…give it a whirl?

I’ll stop there. You see how that happened. Anyway, I’ve always wondered when it was the right time to toss yourself into the erotic river, so to speak? Obviously you can’t do that on the first or second date. It just seems that you’d look a little nuts (no pun intended) to mention your affinity for being spanked on the first date lest you want that guy to only view you as a sex toy.

But there has to be some point where it’s totally fine to say, “hey baby, I’m trying to get my ass tickled with the AssTickler. You down?” I think if you’re in a committed relationship with somebody that should be fair game…since they are kind of obligated to NOT put your business in the street until you break up and even then you still have plausible deniability.

Or what if a woman wants to bring in the Rabbit or *CENSORED* not as a replacement but an enhancer. Is that something you definitely have to do only within the confines of a relationship? I kind of think so but its possible that I’m just a prude. Shucks, I remember being taken aback the first time a chick brought some KY Jelly into my home. I was like…”for shame, fair maiden, whatever shall we do with this!” Granted we weren’t together, but I also didn’t judge her for it either. And that stuff was intense. Not the jelly, we didn’t get the KY Intense, just the smangage using the old fashioned. Odd experiences all around.

What was I talking about?

So yeah, question, when is it appropriate to ask for certain less than conservative sexual acts, etc with somebody? Can you do it while you’re only dating or does it have to be within a relationship?

What say you good people?

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Alex Wise served over 5 years as relationship expert helping women from around the world figure out the men in their love lives from an honest, male perspective. Alex is one of the contributors and editors for Loveawake.com dating website. He is passionate about thought leadership writing, and regularly contributes to various career, social media, public relations, branding, and online dating communities.